:Amixetrine
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 451555297
| IUPAC_name = 1-[2-(3-methylbutoxy)-2-phenylethyl]pyrrolidine
| image = Amixetrine.png
| tradename =
| pregnancy_category =
| legal_status = Rx-only
| routes_of_administration = Oral
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 24622-72-8
| ATC_prefix = none
| ATC_suffix =
| PubChem = 71911
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 64922
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104080
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7UL287YTPJ
| C=17 | H=27 | N=1 | O=1
| smiles = O(CCC(C)C)C(c1ccccc1)CN2CCCC2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H27NO/c1-15(2)10-13-19-17(14-18-11-6-7-12-18)16-8-4-3-5-9-16/h3-5,8-9,15,17H,6-7,10-14H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ISRODTBNJUAWEJ-UHFFFAOYSA-N
}}
Amixetrine (INN; brand name Somagest; developmental code CERM-898) is a drug that was formerly marketed in France but is now no longer sold.{{cite book | vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA80|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=80–}}{{cite book|author=William Andrew Publishing| chapter = Amixetrine Hydrochloride |title=Pharmaceutical Manufacturing Encyclopedia | edition = 3rd| chapter-url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA285|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=285–}} According to various sources it has been said to be an anti-inflammatory, antidepressant, antispasmodic, anticholinergic, antihistamine, and antiserotonergic, but its definitive indications and pharmacology are unclear. The drug was first synthesized in 1969 and was introduced in France in 1972.
Synthesis
The treatment of isoamyl alcohol (1) with styrene (2) at -10 °C with dropwise addition of tert-butyl hypobromite gives (2-bromo-1-(isopentyloxy)ethyl)benzene (3).{{Cite patent|GB|1253818}} idem Mauvernay Roland Yves, Norbert Busch, DE1811767A1 (1969 to Ct Europ De Rech S Mauvernay){{cite book | doi = 10.1002/047084289X.rb387.pub2 | isbn = 978-0-470-84289-8 | title = Encyclopedia of Reagents for Organic Synthesis | chapter = -Butyl Hypobromite | date = 2009 | publisher = John Wiley & Sons }} Displacement of the halogen leaving group by pyrrolidine completes the synthesis of amixetrine (4).